3-Iodo-4-methylbenzoic acid → Ethyl 3-iodo-4-methylbenzoate

HRID 1527890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527890
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](OCC)(=O)[CH3:13].CCCCCC>C(O)C.S(=O)(=O)(O)O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:12][CH3:13])=[O:6]

Komponenten

5

Edukt 2

HCID 6216403-Iodo-4-methylbenzoic acidHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 23073518Ethyl 3-iodo-4-methylbenzoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of 3-iodo-4-methylbenzoic acid (1.5 g, 5.7 mmol) in 25 ml of ethanol was dropped in 0.5 ml of concentrated sulfuric acid. The reaction was refluxed overnight. TLC (Ethyl Acetate/Hexane 1:10) indicated the completion of the esterification. The extra ethanol was evaporated and the residue was dissolved in 30 ml of dichloromethane, which was washed with water (10 ml) and brine (10 ml), dried, and evaporated to a thick oil. A white solid was obtained after drying under vacuo (1.56 g, in 95% yield).

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. customThe extra ethanol was evaporated
  3. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  4. washwhich was washed with water (10 ml) and brine (10 ml)
  5. customdried
  6. customevaporated to a thick oil
  7. customA white solid was obtained
  8. customafter drying under vacuo (1.56 g, in 95% yield)

Quellen und Nachweise

ORD-Eintrag
ord-f5b310a012ff4175b02236ce5a9e74e7
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090561B2

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